Polymer electrolytes and process for their production

Details Polymer electrolytes and process for their production Polymer electrolytes and process for their production

1998-06-24

2000-08-01

Truong, Duc

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From sulfur-containing reactant

528373, 528486, 528487, 528500, 528503, C08G 7504, C08F 610, C08J 314

Patent

active

060968567

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to compounds of the polyarylene sulfide-sulfonic acid class which have a good solubility in polar aprotic solvents, their use, and a process for the preparation of such polyarylene sulfide-sulfonic acids.
Polyarylene sulfide, in particular poly-p-phenylene sulfide, is known as a polymer which is distinguished by a particular resistance in respect of chemical and thermal influences. However, in order to be able to use this polymer for applications in aqueous media, it is expedient to increase its hydrophilicity. A method for achieving this aim by means of a sulfonation reaction is described in U.S. Pat. No. 4,110,265. In this method polyphenylene sulfide is reacted with oleum to give a sulfonated product which is employed as a cation exchanger material. Nevertheless, this material is described as a completely insoluble and furthermore also non-fusible crosslinked polymer, which makes any further processing of this material very difficult. U.S. Pat. No. 4,199,321 describes the improvement in the dyeability of PPS fibers by sulfonation with H.sub.2 SO.sub.4, SO.sub.3 and oleum. However, the fibers described here are sulfonated only on their surface.
The present invention was based on the object of providing a possibility, starting from customary polyarylene sulfides, of preparing polymers therefrom, by modification, which are soluble in polar aprotic solvents and which, for example, can easily be further processed to films. Another object comprises preparation of cation exchangers which are soluble in polar aprotic solvents starting from customary polyarylene sulfides.
This object is achieved by a polyarylene sulfide-sulfonic acid, the characterizing feature of which is to be seen in that it is soluble in polar aprotic solvents.
Examples of polar aprotic solvents which may be mentioned are N-methylpyrrolidone (NMP), dimethylacetamide (DMAC), dimethyl sulfoxide (DMSO) or dimethylformamide (DMF).
Suitable polyarylene sulfides in the context of the present invention are generally polymers of which the main chain is formed from the recurring units of the form
Ar in the formula is 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, biphenylene, naphthylene, anthrylene or another bivalent aromatic unit. The average molecular weights M.sub.w of suitable polyarylene sulfides are preferably in the range from 2000 to 200 000 g/mol. Poly-p-phenylene sulfide which has an average molecular weight M.sub.w of >50 000 g/mol and in which the aromatic unit is exclusively 1,4-phenylene, which can be detected by .sup.1 H-NMR spectroscopy, is particularly preferably employed in the context of the present invention. Furthermore, those poly-[1,4-phenylene sulfide]s which are crosslinked to a limited extent, but nevertheless are fusible and soluble, are used. The particularly preferred polyarylene sulfides have become known on the market under the brand names .RTM.Fortron (Fortron Industries) or .RTM.Ryton (Phillips Petroleum).
A polyarylene sulfide-sulfonic acid in the context of the present invention is to be understood as meaning a polymer which is sulfonated to an extent of 0.1 to 100 mol %, preferably 2 to 40 mol %, based on the total amount of recurring units, i.e. the aromatic units carry sulfonic acid radicals (--SO.sub.3 H). Furthermore, the aromatic units can be chlorinated to an extent of 0 to 40 mol %, preferably 5 to 25 mol %, based on the total amount of recurring units, and the sulfide bridges between the aromatic units can be oxidized to sulfoxide to an extent of 0 to 100 mol %, likewise based on the total amount of recurring units.
The following structural formulae show examples of recurring units which the polyarylene sulfide-sulfonic acid referred to can contain. ##STR1##
The polyarylene sulfide-sulfonic acid according to the invention dissolves in N-methyl-pyrrolidone in an amount of more than 5% by weight, the soluble polyarylene sulfide-sulfonic acid having an average molecular weight of 2000 to 200 000 g/mol, preferably .gtoreq.20 000 to 100 000 g/mol.
The process for the preparation

REFERENCES:
patent: 3948865 (1976-04-01), Brady et al.
patent: 4110265 (1978-08-01), Hodgdon
patent: 4199321 (1980-04-01), Blackwell et al.
patent: 5153305 (1992-10-01), Tsuchida et al.
Journal of Polymer Science Part A: Polymer Chemistry Edition 27 (1980) Aug., No. 9, New York, U.S., pp. 3043-3051.
Polymers for Advanced Technologies 5 (1994) Jun., No. 6, Chichester, Sussex, GB, pp. 309-312.

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